AI Article Synopsis
- The work presents a novel method for synthesizing oligonucleotides that include a modified uridine, specifically a difluorophosphonylated allylic ether at the 2'-position.
- Efficient synthesis of fluorinated homouridylates and miR-342-3p analogs was achieved, showing these new oligonucleotides possess good thermal stability and increased lipophilicity.
- Comparison with other oligonucleotides indicates that the improved chemical properties are due to the difluoromethylphosphonate group present in the new synthesis.
Article Abstract
The first synthesis of oligonucleotides incorporating U, a uridine modified with a difluorophosphonylated allylic ether onto the 2'-position, is described. Fluorinated homouridylates and miR-342-3p analogues are efficiently prepared. UV-melting experiments and enzymatic degradation studies indicate this new series of fluorinated oligonucleotides exhibit good and thermal metabolic stability as well as an increased lipophilicity. Comparison with oligonucleotides containing 2'- O-allyluridine instead of U reveals improvement of these chemical properties is related to the presence of the difluoromethylphosphonate group.
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Article Synopsis
- The work presents a novel method for synthesizing oligonucleotides that include a modified uridine, specifically a difluorophosphonylated allylic ether at the 2'-position.
- Efficient synthesis of fluorinated homouridylates and miR-342-3p analogs was achieved, showing these new oligonucleotides possess good thermal stability and increased lipophilicity.
- Comparison with other oligonucleotides indicates that the improved chemical properties are due to the difluoromethylphosphonate group present in the new synthesis.
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